Ask a chief executive what is on their mind and you will get the strategy, the quarter, the board. Ask them what they have been putting off and, more often than not, the answer is a person.
Not a bad person. Usually someone who was right for the company at a smaller size, or someone who is excellent at four fifths of the job and quietly destructive in the fifth, or someone who was loyal at a moment when loyalty was scarce and is now being repaid with a role they cannot do.
The conversation has been due for months. Everyone senior knows. Nothing happens.
Why it stays stuck
The usual explanation is that the leader is conflict averse. Sometimes true, rarely the whole story.
More often the delay is doing something for you. While the conversation has not happened, the situation is still ambiguous, and ambiguity is comfortable. There is a version of the future where they turn it around. There is a version where the new structure makes the problem disappear without anyone having to say anything. There is a version where they leave on their own and you never have to be the person who did it.
None of these are likely. All of them are available, and they remain available for exactly as long as you do not act.
There is also the debt. If this person was there early, or covered for you once, or took the job when nobody else would, then the conversation is not just difficult, it feels ungrateful. That feeling is real and it should be respected. It is also not a reason. Gratitude is a thing you can express in a dozen ways, and leaving someone in a role they are failing at is not one of them.
What the delay is teaching
Here is the part that is easy to miss from inside it. The delay is not neutral, and it is not private.
The people around that person can see the gap between the standard you describe and the standard you enforce. Every month the gap stays open, it teaches them something about what is actually required here. Your best people learn it fastest, because they are the ones carrying the difference.
You are not protecting one person. You are running an experiment on everyone who is watching you not act.
I have seen a strong second layer quietly disassemble itself over an unaddressed peer. Nobody resigned in protest. They just stopped putting things forward, because the evidence in front of them said that performance was not the thing that determined outcomes here.
The other possibility
Before the obvious conclusion, there is a question worth asking honestly, and it goes the other way.
Have they been told? Not hinted at in a review, not addressed obliquely in a team meeting, not raised through someone else. Told plainly, by you, with specifics, and with a clear statement of what would need to be different.
A surprising number of these situations have never had that conversation. The leader believes it has been had, because they have rehearsed it so many times it feels like it happened. From the other side, the person has received a series of signals they have interpreted, reasonably, as everything being basically fine.
If that is where you are, the next conversation is not an exit conversation. It is the first honest one, and it deserves to be treated as a real opportunity rather than a formality on the way to a decision you have already made.
If they have been told
Then the question is only about timing, and the honest answer is almost always sooner than you want.
One thing that helps, and it is not a technique so much as a reframe. You are not deciding whether they are a good person, which they may well be, and you are not passing judgment on their whole professional life. You are deciding whether this role, at this size, in this year, is the right place for them. Those are different questions and the second one is answerable.
The other thing worth knowing: nobody who has done this has ever told me afterwards that they wished they had waited longer. The regret runs in one direction, consistently enough that I have stopped treating it as anecdote.